The Bot That Broke
Richard Ilott once watched a chatbot become a screenshot. It didn’t crash, and it didn’t give wrong answers—it simply lacked design. Left to its own deterministic devices, the system locked a customer into an infuriating loop of polite, unhelpful interrogation until the user snapped, took a screenshot, and posted it for the internet to mock.
That moment of breakdown sparked a realization: conversation is not an engineering problem, a training data problem, or a linguistics problem. Conversation is a design medium.
In Designing with AI, senior product designer Richard Ilott moves beyond the hype to treat conversation design as a core discipline for product designers of all levels. This isn’t a book for computational linguists or AI researchers—it’s for practitioners shipping real products at scale who want to shape how machines talk to humans.
Drawing on eight years of experience building high-transactional digital products for FTSE 100 businesses, Ilott introduces The 4-Layer Experience Framework and The Anatomy of Conversation. These practical frameworks translate your existing UX thinking into natural language interfaces, proving that the shift from pixels to dialogue doesn't change why we design—only how we execute.
Whether you are designing structured deterministic trees, steering generative AI agents, or navigating your role in the LLM ecosystem, this book provides the mental models, "steering moves," and ready-to-use frameworks to design experiences rooted in human empathy, not machine technicality.
Stop treating conversation like a text box and start designing language as an interface.
The Bot That Broke
Richard Ilott once watched a chatbot become a screenshot. It didn’t crash, and it didn’t give wrong answers—it simply lacked design. Left to its own deterministic devices, the system locked a customer into an infuriating loop of polite, unhelpful interrogation until the user snapped, took a screenshot, and posted it for the internet to mock.
That moment of breakdown sparked a realization: conversation is not an engineering problem, a training data problem, or a linguistics problem. Conversation is a design medium.
In Designing with AI, senior product designer Richard Ilott moves beyond the hype to treat conversation design as a core discipline for product designers of all levels. This isn’t a book for computational linguists or AI researchers—it’s for practitioners shipping real products at scale who want to shape how machines talk to humans.
Drawing on eight years of experience building high-transactional digital products for FTSE 100 businesses, Ilott introduces The 4-Layer Experience Framework and The Anatomy of Conversation. These practical frameworks translate your existing UX thinking into natural language interfaces, proving that the shift from pixels to dialogue doesn't change why we design—only how we execute.
Whether you are designing structured deterministic trees, steering generative AI agents, or navigating your role in the LLM ecosystem, this book provides the mental models, "steering moves," and ready-to-use frameworks to design experiences rooted in human empathy, not machine technicality.
Stop treating conversation like a text box and start designing language as an interface.